KR20230015360A - Compounds, light-emitting materials and light-emitting devices - Google Patents

Abstract

It is to provide an excellent light emitting material. A compound represented by the following general formula is used as a light emitting material. R is a hydrogen atom, a deuterium atom, an aryl group or a heteroaryl group bonded to a carbon atom, Ar is an aryl group or a heteroaryl group bonded to a carbon atom, D ¹ and D ² are donor groups, and at least one is a heterocyclic condensed carbazole -9- It's a diary.

Description

Compounds, light-emitting materials and light-emitting devices

The present invention relates to a compound useful as a light emitting material and a light emitting element using the same.

BACKGROUND OF THE INVENTION Research on improving the luminous efficiency of light emitting elements such as organic electroluminescence elements (organic EL elements) is being actively conducted. In particular, various studies have been conducted to increase luminous efficiency by newly developing and combining electron transport materials, hole transport materials, light emitting materials, and the like constituting organic electroluminescent devices. Among them, research on organic electroluminescent devices using delayed fluorescent materials can also be seen.

A delayed fluorescent material is a material that emits fluorescence when returning from the excited singlet state to the ground state after generating inverse intersystem crossing from the triplet excited state to the singlet excited state in an excited state. Fluorescence by this pathway is called delayed fluorescence because it is observed later than fluorescence (normal fluorescence) from an excited singlet state directly generated from the ground state. Here, for example, when a luminescent compound is excited by injection of a carrier, since the probability of occurrence of a singlet excited state and a triplet excited state is statistically 25%:75%, There is a limit to the improvement of luminous efficiency only with fluorescence. On the other hand, in the delayed fluorescent material, since not only the excited singlet state but also the triplet excited state can be used for fluorescence emission by the path through the above inverse intersystem crossing, higher luminous efficiency is obtained than that of ordinary fluorescent materials. .

After this principle was clarified, various delayed fluorescent materials have been discovered through various studies. However, a material that emits delayed fluorescence is not immediately useful as a light emitting material. Among the delayed fluorescence materials, there are those in which inverse intersystem crossing is relatively difficult to occur, and there are also those with a long lifetime of delayed fluorescence. In addition, in a high current density region, excitons accumulate and the luminous efficiency decreases, or when driving is continued for a long time, it rapidly deteriorates. Therefore, in terms of practicality, there are many delayed fluorescent materials that have room for improvement. For this reason, it has been pointed out that benzonitrile-based compounds known as delayed fluorescent materials also have problems. For example, a compound having the following structure is a material that emits delayed fluorescence (refer to Patent Literature 1), but has problems in that the lifetime of the delayed fluorescence is long and the durability of the device is insufficient.

[Formula 1]

Patent Document 1: WO2014/208698A1

Although it has been pointed out that such problems are encountered, it is difficult to say that sufficient elucidation has been made on the relationship between the chemical structure and characteristics of delayed fluorescent materials. For this reason, it is currently difficult to generalize the chemical structure of a compound useful as a light emitting material, and there are many unclear points.

Under such circumstances, the inventors of the present invention have conducted researches for the purpose of providing more useful compounds as light emitting materials for light emitting elements. And, intensive examination was advanced with the aim of deriving and generalizing the general formula of a more useful compound as a light emitting material.

As a result of intensive studies to achieve the above object, the present inventors have found that among isophthalonitrile derivatives, compounds having a structure satisfying specific conditions are useful as light emitting materials. The present invention has been proposed based on these findings, and specifically has the following configurations.

[One]

A compound represented by the following general formula (1).

[Formula 2]

[In Formula (1),

R is a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded to a carbon atom;

Ar is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded with a carbon atom;

D ¹ and D ² each independently represent a donor group, and at least one of them is a heterocyclic condensed carbazol-9-yl group (the heterocyclic ring and the carbazole may be substituted).]

[2]

The compound according to [1], wherein the compound is represented by the following general formula (2).

[Formula 3]

[3]

The compound according to [1], wherein the compound is represented by the following general formula (3).

[Formula 4]

[4]

The compound according to any one of [1] to [3], wherein D ¹ and D ² are the same.

[5]

The compound according to any one of [1] to [3], wherein D ¹ and D ² are different.

[6]

The heterocyclic ring condensed with the carbazol-9-yl group of the heterocyclic condensed carbazol-9-yl group is a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted pyrrole ring, The compound according to any one of [1] to [5], wherein another ring may be further condensed with the furan ring, the thiophene ring, and the pyrrole ring.

[7]

The compound according to any one of [1] to [6], wherein the heterocyclic condensed carbazol-9-yl group has any one of the following structures.

[Formula 5]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed.]

[8]

The compound according to any one of [1] to [6], wherein the heterocyclic condensed carbazol-9-yl group has any one of the following structures.

[Formula 6]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed.]

[9]

The compound according to any one of [1] to [6], wherein the heterocyclic condensed carbazol-9-yl group has any one of the following structures.

[Formula 7]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed. R' represents a hydrogen atom, a deuterium atom or a substituent.]

[10]

To the carbazol-9-yl group of the heterocyclic condensed carbazol-9-yl group, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, and a substituted or unsubstituted pyrrole ring (the furan ring, the above The compound according to any one of [1] to [9], wherein two heterocycles selected from the group consisting of a thiophene ring and the pyrrole ring may further be condensed with other rings are condensed.

[11]

The compound according to any one of [1] to [10], wherein the heterocyclic condensed carbazol-9-yl group has a structure in which a heterocyclic ring is condensed at the 1st and 2nd positions of the carbazole ring.

[12]

The compound according to any one of [1] to [10], wherein the heterocyclic condensed carbazol-9-yl group has a structure in which a heterocyclic ring is condensed at the 2nd and 3rd positions of the carbazole ring.

[13]

The compound according to any one of [1] to [10], wherein the heterocyclic condensed carbazol-9-yl group has a structure in which a heterocyclic ring is condensed at the 3rd and 4th positions of the carbazole ring.

[14]

The compound according to any one of [1] to [13], wherein R and Ar are different.

[15]

The compound according to any one of [1] to [13], wherein R is a hydrogen atom or a deuterium atom.

[16]

The compound according to any one of [1] to [15], wherein Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group.

[17]

The compound according to any one of [1] to [16], comprising an atom selected from the group consisting of a carbon atom, a hydrogen atom, a heavy hydrogen atom, a nitrogen atom, an oxygen atom, and a sulfur atom.

[18]

A light emitting material comprising the compound according to any one of [1] to [17].

[19]

A light-emitting device characterized by comprising the compound according to any one of [1] to [17].

[20]

The light-emitting element according to [19], wherein the light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a host material.

[21]

The light-emitting element according to [20], wherein the light-emitting element has a light-emitting layer, the light-emitting layer contains the compound and a light-emitting material, and mainly emits light from the light-emitting material.

The compound of the present invention is useful as a light emitting material. Also, among the compounds of the present invention, compounds having a short delayed fluorescence lifetime are included. In addition, an organic light emitting device using the compound of the present invention has high device durability and is useful.

1 is a schematic cross-sectional view showing an example of a layer configuration of an organic electroluminescent element.

Below, the content of this invention is demonstrated in detail. The description of the constitutional requirements described below may be made based on typical embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples. In addition, the numerical range expressed using "-" in this specification means the range which includes the numerical value described before and after "-" as a lower limit and an upper limit. In addition, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention may be replaced with deuterium atoms ( ² H, deuterium D). In the chemical structural formula of this specification, a hydrogen atom is indicated as H or its indication is omitted. For example, when the display of the atom bonded to the ring skeleton constituent carbon atom of the benzene ring is omitted, it is assumed that H is bonded to the ring skeleton constituent carbon atom at the location where the display is omitted. In the chemical structural formula of this specification, a deuterium atom is represented by D.

[Compound represented by general formula (1)]

[Formula 8]

At least one of D ¹ and D ² in General Formula (1) represents a heterocyclic condensed carbazol-9-yl group. The heterocyclic ring and the carbazole ring constituting the heterocyclic condensed carbazol-9-yl group may or may not be substituted, respectively.

The number of heterocycles condensed with the carbazol-9-yl group is one or more, preferably one or two, more preferably one. When two or more heterocycles are condensed, those heterocycles may be the same or different. In one aspect of the present invention, the heterocycle is condensed at the 1st and 2nd positions of the carbazol-9-yl group. In another aspect of the present invention, the heterocycle is condensed at the 2nd and 3rd positions of the carbazol-9-yl group. In another aspect of the present invention, the heterocycle is condensed at the 3rd and 4th positions of the carbazol-9-yl group.

The heterocycle condensed with the carbazol-9-yl group is a ring containing a hetero atom. The hetero atom is preferably selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and more preferably is selected from an oxygen atom, a sulfur atom, and a nitrogen atom. In one preferred aspect, the hetero atom is an oxygen atom. In another preferred aspect, the hetero atom is a sulfur atom. In another preferred aspect, the hetero atom is a nitrogen atom. The number of heteroatoms contained as ring skeleton constituent atoms of the heterocyclic ring is one or more, preferably 1 to 3, and more preferably 1 or 2. In a preferred aspect, the number of heteroatoms is one. When the number of heteroatoms is two or more, it is preferable that they are heteroatoms of the same kind, but they may be constituted by heteroatoms of different kinds. For example, all 2 or more heteroatoms may be nitrogen atoms. Ring skeleton constituent atoms other than heteroatoms are carbon atoms.

The number of ring skeleton constituting atoms constituting the heterocyclic ring fused to the carbazol-9-yl group is preferably 4 to 8, more preferably 5 to 7, and even more preferably 5 or 6. In a preferred aspect, the number of atoms constituting the ring skeleton constituting the heterocycle is 5. It is preferable that two or more conjugated double bonds exist in the heterocyclic ring, and it is preferable that the conjugated system of the carbazole ring is expanded by condensation of the heterocyclic ring (preferably aromatic). Preferred examples of the heterocyclic ring include a furan ring, a thiophene ring, and a pyrrole ring.

Other rings may be further condensed to the heterocyclic ring condensed with the carbazol-9-yl group. In addition, the condensed ring may be a monocyclic ring or a condensed ring. Examples of the condensed ring include an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle. A benzene ring is mentioned as an aromatic hydrocarbon ring. As an aromatic heterocycle, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring are mentioned. As an aliphatic hydrocarbon ring, a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring are mentioned. As an aliphatic heterocycle, a piperidine ring, a pyrrolidine ring, and an imidazoline ring are mentioned. Specific examples of the condensed ring include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyran ring, a tetracene ring, an indole ring, an isoindole ring, a benzimidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, A quinoxaline ring and a cinnoline ring are mentioned.

In a preferred aspect of the present invention, the heterocyclic condensed carbazol-9-yl group is a benzofuran condensed carbazol-9-yl group, a benzothiophene condensed carbazol-9-yl group, an indole condensed carbazol-9-yl group, or It is a silaindene condensed carbazol-9-yl group. In a more preferred aspect of the present invention, the heterocyclic condensed carbazol-9-yl group is a benzofuran condensed carbazol-9-yl group, a benzothiophene condensed carbazol-9-yl group, or an indole condensed carbazol-9-yl group. am.

In the present invention, as the benzofuran condensed carbazol-9-yl group, a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be employed. In addition, a substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be employed.

A preferred benzofuran condensed carbazol-9-yl group is a carbazol-9-yl group in which only one benzofuran ring is condensed at the 2nd and 3rd positions and no other heterocyclic ring is condensed (the benzene ring may be condensed). Specifically, it is a group having any one of the following structures, and the hydrogen atom in the following structures may be substituted. Preferred examples include those in which some of the hydrogen atoms in the following structure are substituted with deuterium atoms, and those in which all of the hydrogen atoms in the following structure are substituted with deuterium atoms. Unsubstituted ones can also be preferably employed.

[Formula 9]

A carbazol-9-yl group in which two benzofuran rings are condensed at the 2nd and 3rd positions and the heterocyclic ring is not condensed is also preferable (the benzene ring may be condensed). Specifically, it is a group having any one of the following structures, and the hydrogen atom in the following structures may be substituted. Preferred examples include those in which some of the hydrogen atoms in the following structure are substituted with deuterium atoms, and those in which all of the hydrogen atoms in the following structure are substituted with deuterium atoms. Unsubstituted ones can also be preferably employed.

[Formula 10]

In the present invention, as the benzothiophene condensed carbazol-9-yl group, a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be employed. In addition, a substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be employed.

A preferred benzothiophene condensed carbazol-9-yl group is a carbazol-9-yl group in which only one benzothiophene ring is condensed at the 2nd and 3rd positions and no other heterocyclic ring is condensed (the benzene ring may be condensed). Specifically, it is a group having any one of the following structures, and the hydrogen atom in the following structures may be substituted. Preferred examples include those in which some of the hydrogen atoms in the following structure are substituted with deuterium atoms, and those in which all of the hydrogen atoms in the following structure are substituted with deuterium atoms. Unsubstituted ones can also be preferably employed.

[Formula 11]

A carbazol-9-yl group in which two benzothiophene rings are condensed at the 2nd and 3rd positions and the heterocyclic ring is not condensed is also preferable (the benzene ring may be condensed). Specifically, it is a group having any one of the following structures, and the hydrogen atom in the following structures may be substituted. Preferred examples include those in which some of the hydrogen atoms in the following structure are substituted with deuterium atoms, and those in which all of the hydrogen atoms in the following structure are substituted with deuterium atoms. Unsubstituted ones can also be preferably employed.

[Formula 12]

In the present invention, as the indole condensed carbazol-9-yl group, a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl group can be employed. In addition, a substituted or unsubstituted indolo[3,2-a]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted indolo[3,2-b]carbazol-9-yl group can also be employed. In addition, a substituted or unsubstituted indolo[2,3-c]carbazol-9-yl group can also be employed. A substituted or unsubstituted indolo[3,2-c]carbazol-9-yl group can also be employed.

A preferable indole condensed carbazol-9-yl group is a carbazol-9-yl group in which only one indole ring is condensed at the 2nd and 3rd positions and no other heterocyclic ring is condensed (the benzene ring may be condensed). Specifically, it is a group having any of the following structures, and R' in the following structures represents a hydrogen atom, a heavy hydrogen atom or a substituent (preferably R' is a substituent). R' is preferably a substituted or unsubstituted aryl group. The hydrogen atom in the following structure may be substituted. Preferred examples include those in which some of the hydrogen atoms in the following structure are substituted with deuterium atoms, and those in which all of the hydrogen atoms in the following structure are substituted with deuterium atoms. Unsubstituted ones can also be preferably employed.

[Formula 13]

The heterocyclic ring and carbazole ring constituting the heterocyclic condensed carbazol-9-yl group may be substituted, respectively. When substituted, it may be substituted with a deuterium atom or may be substituted with a substituent other than that. Examples of the substituent here include an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, and a cyano group. These substituents may be substituted with another substituent. For example, aspects substituted with a heavy hydrogen atom, an alkyl group, an aryl group, an alkoxy group, or an alkylthio group are exemplified.

The "alkyl group" used herein may be linear, branched, or cyclic. Moreover, 2 or more types of a linear part, a cyclic part, and a branch part may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Moreover, carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. As specific examples of the alkyl group, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group , 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group , a cycloheptyl group. The alkyl group as a substituent may be further substituted with a heavy hydrogen atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom.

The "alkenyl group" may be linear, branched or cyclic. Moreover, 2 or more types of a linear part, a cyclic part, and a branch part may be mixed. The number of carbon atoms in the alkenyl group can be, for example, 2 or more or 4 or more. Moreover, carbon number can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. As specific examples of the alkenyl group, ethenyl group, n-propenyl group, isopropenyl group, n-butenyl group, isobutenyl group, n-pentenyl group, isopentenyl group, n-hexenyl group, isohexenyl group, 2- An ethylhexenyl group is mentioned. The alkenyl group that is a substituent may be further substituted.

"Aryl group" and "heteroaryl group" may be a monocyclic ring or a condensed ring in which two or more rings are condensed. In the case of a condensed ring, the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example. Specific examples of the ring include a benzene ring, a pyridine ring, a pyrimidine ring, a triazine ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a triphenylene ring, a quinoline ring, a pyrazine ring, a quinoxaline ring, and a naphthyridine ring. . As specific examples of the arylene group or heteroarylene group, phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-pyridyl group, 3-pyridyl group, 4- A pyridyl group is mentioned.

For the alkyl part of the "alkoxy group" and "alkylthio group", reference can be made to the description and specific examples of the above alkyl group. For the aryl part of the "aryloxy group" and "arylthio group", reference can be made to the description and specific examples of the above aryl group. For the heteroaryl moiety of "heteroaryloxy group" and "heteroarylthio group", the description and specific examples of the above heteroaryl group can be referred to.

The heterocyclic condensed carbazol-9-yl group preferably has 16 or more atoms, more preferably 20 or more, for example, 16 or more atoms other than hydrogen atoms and deuterium atoms. Moreover, it is preferable that it is 80 or less, it is more preferable that it is 50 or less, and it is still more preferable that it is 30 or less.

In the general formula (1), the heterocyclic condensed carbazol-9-yl group may be only D ¹ or only D ² . In a preferred aspect of the present invention, both D ¹ and D ² are heterocyclic condensed carbazol-9-yl groups. At this time, D ¹ and D ² may have the same structure or may be heterocyclic condensed carbazol-9-yl groups different from each other.

When only one of D ¹ and D ² is a heterocyclic condensed carbazol-9-yl group, the other is a donor group other than the heterocyclic condensed carbazol-9-yl group (hereinafter referred to as “another donor group”). The other donor group referred to herein is a group having a negative Hammett σp value. Here, "Hamett's σp value" was proposed by LP Hammett, and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following formula established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:

log(k/k ₀ )=ρσp

or

log(K/K ₀ )=ρσp

It is a constant (σp) specific to the substituent in . In the above formula, k is the rate constant of the benzene derivative without a substituent, k ₀ is the rate constant of the benzene derivative substituted with a substituent, K is the equilibrium constant of the benzene derivative without a substituent, K ₀ is the benzene substituted with a substituent The equilibrium constant of the derivative, ρ, represents the reaction constant determined by the type and conditions of the reaction. For the description of "Hamet's σp value" and the numerical value of each substituent in the present invention, Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991) can be referred to the description of the σp value. Groups with a negative Hammett σp value tend to exhibit electron donating properties (donor properties), and groups with a positive Hammett σp value tend to exhibit electron withdrawing properties (acceptor properties).

It is preferable that another donor group in this invention is a group containing a substituted amino group. The substituent bonded to the nitrogen atom of the amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and is substituted or unsubstituted. It is more preferable that it is an aryl group of , or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The donor group in the present invention may be a group bonded to a nitrogen atom of a substituted amino group, or a group bonded to a group bonded to a substituted amino group. The group to which the substituted amino group bonds is preferably a π conjugated group. More preferable is a group bonded to the nitrogen atom of the substituted amino group. For the alkyl group, alkenyl group, aryl group and heteroaryl group which are the substituents referred to herein, the above corresponding descriptions regarding substituents of aromatic hydrocarbon ring groups and aromatic heterocyclic groups can be referred to.

Particularly preferable as another donor group in the present invention is a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group may further condense a benzene ring or a hetero ring (except for a benzofuran ring, a benzothiophene ring, an indole ring, an indene ring, and a silaindene ring). Examples of the substituent for the carbazol-9-yl group include an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, and a substituted amino group. Examples of preferable substituents include an alkyl group, an aryl group, and a substituted amino group. For description of the substituted amino group, the description of the previous paragraph can be referred to. The substituted amino group referred to herein includes a substituted or unsubstituted carbazolyl group, and includes, for example, a substituted or unsubstituted carbazol-3-yl group and a substituted or unsubstituted carbazol-9-yl group.

It is preferable that the number of atoms other than a hydrogen atom and a deuterium atom of another donor group in this invention is 8 or more, and it is more preferable that it is 12 or more, and, for example, it can also be set to 16 or more. Moreover, it is preferable that it is 80 or less, it is more preferable that it is 60 or less, and it is more preferable that it is 40 or less.

Below, the specific example of the donor group which can be employ|adopted for D1 and D2 ^of General formula ( ¹ ) is shown. D13 to D78, D84 to D119, D150 to D161, D168 to D209, D215 to D268, D270 to D324 are specific examples of heterocyclic condensed carbazol-9-yl groups, D1 to D12, D79 to 83, D120 to 149, D162 to D167, D210 to D214, and D269 are specific examples of other donor groups. In the structural formulas below, Ph represents a phenyl group, and * represents a bonding position.

[Formula 14-1]

[Formula 14-2]

[Formula 14-3]

[Formula 14-4]

[Formula 14-5]

[Formula 14-6]

[Formula 14-7]

[Formula 14-8]

[Formula 14-9]

[Formula 14-10]

[Formula 14-11]

[Formula 14-12]

[Formula 14-13]

[Formula 14-14]

R in the general formula (1) is a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded to a carbon atom. In a preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom. However, an aspect in which R is a substituted or unsubstituted aryl group or an aspect in which R is a substituted or unsubstituted heteroaryl group bonded to a carbon atom can also be employed. When R is an aryl group, it is preferably a substituted aryl group. Moreover, when R is a heteroaryl group, it is preferable that it is a substituted heteroaryl group.

Ar in the general formula (1) is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded with a carbon atom. In a preferred aspect of the present invention, Ar is a substituted or unsubstituted aryl group. However, an aspect in which Ar is a substituted or unsubstituted heteroaryl group can also be employed.

For descriptions and preferred ranges of the aryl and heteroaryl groups that can be used for R and Ar, the description of aryl and heteroaryl groups in the substituent of the heterocyclic condensed carbazol-9-yl group can be referred to. However, a heteroaryl group is a heteroaryl group bonded with a carbon atom. As the substituent of the aryl group and the substituent of the heteroaryl group, an alkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, between Anogi can be mentioned. These substituents may be substituted with another substituent. As a group of a preferable substituent, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, and a cyano group are mentioned.

In a preferred aspect of the present invention, R is a hydrogen atom or a deuterium atom, Ar is a substituted or unsubstituted phenyl group (the phenyl group includes at least one ring selected from a benzene ring, a pyridine ring, a furan ring, a thiophene ring and a pyrrole ring) may be condensed). In another preferred embodiment of the present invention, R is a hydrogen atom or a deuterium atom, Ar is a substituted or unsubstituted pyridyl group (the pyridyl group is selected from a benzene ring, a pyridine ring, a furan ring, a thiophene ring and a pyrrole ring) One or more rings may be condensed). In another preferred embodiment of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted phenyl group (the phenyl group is substituted with one or more groups selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group). )am. In another preferred embodiment of the present invention, R is a hydrogen atom or a deuterium atom, and Ar is a substituted pyridyl group (the pyridyl group includes at least one group selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted pyridyl group). is replaced).

In the following, specific examples of substituted or unsubstituted aryl groups and substituted or unsubstituted heteroaryl groups bonded to carbon atoms that can be used for R and Ar in Formula (1) are shown. In the structural formulas below, * represents a bonding position.

[Formula 15-1]

[Formula 15-2]

[Formula 15-3]

The compound represented by General Formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. In a preferred aspect of the present invention, the compound represented by the general formula (1) is composed of only atoms selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, and an oxygen atom. Moreover, the compound represented by General formula (1) may be a compound comprised only of atoms selected from the group which consists of a carbon atom, a hydrogen atom, a heavy hydrogen atom, a nitrogen atom, and a sulfur atom. The compound represented by General Formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a hydrogen atom and a nitrogen atom. In addition, the compound represented by General formula (1) may be a compound which does not contain a hydrogen atom but contains a deuterium atom. For example, the compound represented by General Formula (1) may be a compound composed only of atoms selected from the group consisting of a carbon atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom.

In one aspect of the present invention, the compound represented by the general formula (1) has a symmetrical structure.

In a preferable aspect of the present invention, the compound represented by the general formula (1) has a structure represented by the following general formula (2).

[Formula 16]

In a preferable aspect of the present invention, the compound represented by the general formula (1) has a structure represented by the following general formula (3).

[Formula 17]

For definitions and descriptions of R, Ar, D ¹ and D ² in the general formulas (2) and (3), reference can be made to the corresponding description of the general formula (1).

Below, the specific example of the compound represented by General formula (1) is shown. Specific examples are shown by specifying R ¹ to R ⁴ in the following general formula for each compound. R in the general formula (1) corresponds to R ¹ in the general formula below, and D ¹ in the general formula (1) corresponds to R ² in the general formula below. In addition, when rotational isomers exist among the following compounds, the mixture of rotational isomers and each separated rotational isomer are also disclosed herein.

[Formula 18]

[Table 1-1]

[Table 1-2]

[Table 1-3]

[Table 1-4]

[Table 1-5]

[Table 1-6]

[Table 1-7]

[Table 1-8]

[Table 1-9]

[Table 1-10]

[Table 1-11]

[Table 1-12]

[Table 1-13]

[Table 1-14]

[Table 1-15]

[Table 1-16]

[Table 1-17]

[Table 1-18]

[Table 1-19]

[Table 1-20]

[Table 1-21]

[Table 1-22]

[Table 1-23]

[Table 1-24]

[Table 1-25]

[Table 1-26]

[Table 1-27]

Compounds in which H in R ¹ in Compounds 1 to 6300 is substituted with D are sequentially disclosed herein as Compounds 6301 to 12600. Compounds 12601 to 18900 are disclosed herein as compounds 12601 to 18900, in which R ¹ and R ⁴ in compounds 1 to 6300 were replaced to form R ⁴ and R ¹ . Compounds in which H in R ² in Compounds 12601 to 18900 are substituted with D are disclosed herein as Compounds 18901 to 25200 in order. Compounds 25201 to 31500, wherein R ¹ , R ² , R ³ , R ⁴ in Compounds 1 to 6300 were sequentially referred to as R ³ , R ¹ , R ⁴ , R ² are disclosed herein. Compounds in which H in R ³ in Compounds 25201 to 31500 are substituted with D are disclosed herein as Compounds 31501 to 37800 in order. Compounds 37801 to 44100, wherein R ¹ , R ² , R ³ , R ⁴ in Compounds 1 to 6300 were sequentially referred to as R ⁴ , R ¹ , R ² , R ³ , are disclosed herein. Compounds in which H in R ⁴ in Compounds 37801 to 44100 are substituted with D are disclosed herein as Compounds 44101 to 50400 in order. Compounds 50401 to 56700 are disclosed herein as compounds 50401 to 56700, wherein R ¹ , R ³ , and R ⁴ in compounds 1 to 6300 were replaced to form R ³ , R ⁴ , and R ¹ . Compounds in which H in R ³ in Compounds 50401 to 56700 are substituted with D are disclosed herein as Compounds 56701 to 63000 in order. R ³ and R ⁴ in compounds 1 to 6300 are replaced and R ⁴ and R ³ are disclosed herein as compounds 63001 to 69300. Compounds in which H in R ¹ in Compounds 63001 to 69300 are substituted with D are disclosed herein as Compounds 69301 to 75600 in order. Each structure of the above compounds 901 to 75600 is individually specified, and each is described as a specific compound in the present specification.

The molecular weight of the compound represented by the general formula (1) is preferably 1500 or less, and more preferably 1200 or less, in the case of intending to use an organic layer containing the compound represented by the general formula (1) by vapor deposition, for example. It is preferably 1000 or less, more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by General Formula (1). Preferably it is 624 or more.

The compound represented by the general formula (1) may be formed into a film regardless of molecular weight by a coating method. If the coating method is used, it is possible to form a film even with a compound having a relatively large molecular weight. Among cyanobenzene-based compounds, the compound represented by the general formula (1) has the advantage of being easily soluble in organic solvents. For this reason, the compound represented by General formula (1) is easy to apply a coating method and it is easy to refine|purify and raise purity.

Applying the present invention, it is also conceivable to use a compound containing a plurality of structures represented by the general formula (1) in a molecule as a light emitting material.

For example, it is conceivable to make a polymeric group exist in advance in the structure represented by General formula (1), and to use the polymer obtained by polymerizing the polymerizable group as a light emitting material. Specifically, by preparing a monomer containing a polymerizable functional group in any one of Ar, D ¹ , and D ² of Formula (1), and polymerizing this alone or copolymerizing it together with other monomers, It is conceivable to obtain a polymer and use the polymer as a light emitting material. Alternatively, it is also conceivable to obtain dimers and trimers by coupling compounds having a structure represented by General Formula (1), and to use them as a light emitting material.

As an example of the polymer which has a repeating unit containing the structure represented by General formula (1), the polymer containing the structure represented by following General formula (4) or (5) is mentioned.

[Formula 19]

In General Formula (4) or (5), Q represents a group containing a structure represented by General Formula (1), and L ¹ and L ² represent a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, still more preferably 2 to 10. The linking group preferably has a structure represented by -X ¹¹ -L ¹¹ -. Here, X ¹¹ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L ¹¹ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. it is more preferable

In General Formula (4) or (5), R ¹⁰¹ , R ¹⁰² , R ¹⁰³ and R ¹⁰⁴ each independently represents a substituent. Preferably, they are a substituted or unsubstituted alkyl group of 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group of 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group of 1 to 3 carbon atoms or 1 carbon atom. They are an unsubstituted alkoxy group of 3 to 3, a fluorine atom, or a chlorine atom, and more preferably an unsubstituted alkyl group of 1 to 3 carbon atoms or an unsubstituted alkoxy group of 1 to 3 carbon atoms.

The linking group represented by L ¹ and L ² can bind to any one of Ar, D ¹ , and D ² of the general formula (1) constituting Q. Two or more linking groups may be connected to one Q to form a cross-linked structure or network structure.

As a specific structural example of a repeating unit, the structure represented by following formula (6) - (9) is mentioned.

[Formula 20]

A polymer having a repeating unit containing the formulas (6) to (9) is prepared by introducing a hydroxyl group into any one of Ar, D ¹ , and D ² of the general formula (1) and reacting the following compound as a linker. It can be synthesized by introducing a polymerizable group and polymerizing the polymerizable group.

[Formula 21]

The polymer containing the structure represented by General Formula (1) in the molecule may be a polymer composed only of repeating units having a structure represented by General Formula (1), or may be a polymer containing repeating units having a structure other than that. Moreover, a single type may be sufficient as the repeating unit which has the structure represented by General formula (1) contained in a polymer, and 2 or more types may be sufficient as it. As a repeating unit which does not have a structure represented by General formula (1), what is induced|guided|derived from the monomer used for normal copolymerization is mentioned. Examples include repeating units derived from monomers having ethylenically unsaturated bonds such as ethylene and styrene.

In one embodiment, the compound represented by general formula (1) is a light emitting material.

In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence.

In one embodiment of the present disclosure, the compound represented by Formula (1), when excited by thermal or electronic means, in the blue, green, yellow, orange, and red regions of the UV region and the visible spectrum (for example, about 420 nm to about 420 nm) about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or in the near-infrared region.

In one embodiment of the present disclosure, the compound represented by Formula (1), when excited by thermal or electronic means, emits light in a red or orange region (eg, about 620 nm to about 780 nm, about 650 nm) of the visible spectrum. can kick off

In one embodiment of the present disclosure, the compound represented by the general formula (1), when excited by thermal or electronic means, in the orange or yellow region of the visible spectrum (for example, about 570 nm to about 620 nm, about 590 nm, about 570 nm) can emit light from

In one embodiment of the present disclosure, the compound represented by Formula (1), when excited by thermal or electronic means, can emit light in the green region (eg, about 490 nm to about 575 nm, about 510 nm) of the visible spectrum. there is.

In one embodiment of the present disclosure, the compound represented by Formula (1), when excited by thermal or electronic means, can emit light in the blue region (eg, about 400 nm to about 490 nm, about 475 nm) of the visible spectrum. there is.

In one embodiment of the present disclosure, the compound represented by Formula (1) can emit light in the ultraviolet spectrum region (eg, 280 to 400 nm) when excited by thermal or electronic means.

In one embodiment of the present disclosure, the compound represented by the general formula (1) can emit light in the infrared spectrum region (for example, 780 nm to 2 μm) when excited by thermal or electronic means.

The electronic properties of the small molecule chemical substance library can be calculated using quantum chemical calculations based on known ab initio. For example, the Hartree-Fock equation (TD- By analyzing DFT/B3LYP/6-31G*), molecular fragments (parts) having a HOMO above a specific threshold and a LUMO below a specific threshold can be screened.

Thus, when there is a HOMO energy (eg, ionization potential) of, for example, -6.5 eV or more, the donor portion ("D") can be selected. Also, for example, when there is a LUMO energy (for example, electron affinity) of -0.5 eV or less, an acceptor moiety ("A") can be selected. The bridging moiety (“B”) is a strong conjugation system that can, for example, strictly confine the acceptor and donor moieties to specific conformations, thereby preventing overlap between the π conjugated systems of the donor and acceptor moieties from occurring. .

In one embodiment, the compound library is screened using one or more of the following properties.

1. Light emission near a specific wavelength

2. Calculated triplet state above a certain energy level

3. ΔE _ST value below a certain value

4. Quantum yield above a certain value

5. HOMO level

6. LUMO level

In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state (ΔE _ST ) at 77 K is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, the ΔE _ST value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV or about It is less than 0.01eV.

In one embodiment, the compound represented by formula (1) is greater than 25%, for example about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60% , a quantum yield of about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[Synthesis method of compound represented by general formula (1)]

The compound represented by General Formula (1) is a novel compound.

The compound represented by General Formula (1) can be synthesized by combining known reactions. For example, synthesis by reacting D ¹ -H or D ² -H with difluoroisophthalonitrile in which the position where D ¹ or D ² is to be introduced is substituted with a fluorine atom in tetrahydrofuran in the presence of sodium hydride. It is possible. When D ¹ and D ² are different from each other, the reaction with D ¹ -H and D ² -H may be performed in two stages. For specific conditions and reaction procedures of the reaction, reference can be made to the synthesis example described later.

[Constituent using the compound represented by the general formula (1)]

In one embodiment, the same compound is combined with the compound represented by the general formula (1), the same compound is dispersed, the same compound is covalently bonded, the same compound is coated, the same compound is supported, or one that associates with the same compound A solid film or layer is formed by using together with the above materials (for example, small molecules, polymers, metals, metal complexes, etc.). For example, a film can be formed by combining the compound represented by the general formula (1) with an electroactive material. In some cases, you may combine the compound represented by General formula (1) with a hole transport polymer. In some cases, you may combine the compound represented by General formula (1) with an electron transport polymer. In some cases, you may combine the compound represented by General formula (1) with a hole transport polymer and an electron transport polymer. In some cases, the compound represented by Formula (1) may be combined with a copolymer having both a hole transporting portion and an electron transporting portion. According to the above embodiments, electrons and/or holes formed in the solid film or layer can be made to interact with the compound represented by the general formula (1).

[Formation of film]

In one embodiment, the film containing the compound of the present invention represented by General Formula (1) can be formed in a wet process. In the wet process, a solution in which a composition containing the compound of the present invention is dissolved is applied to cotton, and a film is formed after the solvent is removed. Examples of the wet process include, but are not limited to, a spin coating method, a slit coating method, an inkjet method (spray method), a gravure printing method, an offset printing method, and a flexographic printing method. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, a substituent (eg, an alkyl group) that increases solubility in an organic solvent may be introduced into a compound included in the composition.

In one embodiment, a film containing the compound of the present invention can be formed in a dry process. In one embodiment, a vacuum deposition method can be employed as a dry process, but is not limited thereto. In the case of adopting the vacuum evaporation method, the compounds constituting the film may be co-deposited from separate evaporation sources, or may be co-deposited from a single evaporation source in which the compounds are mixed. When a single deposition source is used, a mixed powder obtained by mixing powders of compounds may be used, a compressed molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting each compound and cooling may be used. In one embodiment, co-evaporation is performed under the condition that the deposition rate (weight reduction rate) of a plurality of compounds included in a single deposition source matches or approximately matches, thereby corresponding to the composition ratio of the plurality of compounds included in the deposition source. A film having a composition ratio can be formed. If a plurality of compounds are mixed at the same composition ratio as the composition ratio of the film to be formed and used as the deposition source, a film having a desired composition ratio can be easily formed. In one embodiment, the temperature at which each compound to be co-deposited has the same weight loss rate can be specified, and that temperature can be employed as the temperature at the time of co-deposition.

[Example of use of compound represented by general formula (1)]

Organic Light-Emitting Diodes:

One aspect of the present invention relates to the use of a compound represented by the general formula (1) of the present invention as a light emitting material for an organic light emitting element. In one embodiment, the compound represented by the general formula (1) of the present invention can be effectively used as a light emitting material in a light emitting layer of an organic light emitting element. In one embodiment, the compound represented by Formula (1) contains delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In one embodiment, the present invention provides a delayed phosphor having a structure represented by general formula (1). In one embodiment, the present invention relates to the use of a compound represented by general formula (1) as a delayed phosphor. In one embodiment, the compound represented by the general formula (1) of the present invention can be used as a host material and can be used together with one or more light emitting materials, and the light emitting material may be a fluorescent material, a phosphorescent material, or TADF. . In one embodiment, the compound represented by General Formula (1) can also be used as a hole transport material. In one embodiment, the compound represented by General formula (1) can be used as an electron transport material. In one embodiment, the present invention relates to a method for generating delayed fluorescence from a compound represented by formula (1). In one embodiment, an organic light emitting element containing a compound as a light emitting material emits delayed fluorescence and exhibits high light emission efficiency.

In one embodiment, the light emitting layer contains a compound represented by the general formula (1), and the compound represented by the general formula (1) is oriented parallel to the base material. In one embodiment, the substrate is a film forming surface. In one embodiment, the orientation of the compound represented by the general formula (1) relative to the film formation surface affects the propagation direction of light emitted by the aligning compound, or determines the direction. In one embodiment, the light extraction efficiency from the light emitting layer is improved by aligning the propagation direction of the light emitted by the compound represented by the general formula (1).

One aspect of the present invention relates to an organic light emitting device. In one embodiment, the organic light emitting element includes a light emitting layer. In one embodiment, the light emitting layer contains a compound represented by the general formula (1) as a light emitting material. In one embodiment, the organic light emitting device is an organic light luminescence device (organic PL device). In one embodiment, the organic light emitting element is an organic electroluminescence element (organic EL element). In one embodiment, the compound represented by Formula (1) assists light emission of other light emitting materials included in the light emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by the general formula (1) contained in the light-emitting layer is at the lowest singlet excitation energy level, and the lowest singlet excitation energy level of the host material contained in the light-emitting layer and other light-emitting layers contained in the light-emitting layer It is included between the lowest excitation singlet energy levels of the material.

In one embodiment, the organic light luminescence device includes at least one light emitting layer. In one embodiment, an organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer contains at least a light emitting layer. In one embodiment, the organic layer includes only the light emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light emitting layer. Examples of the organic layer include a hole transport layer, a hole injection layer, an electron barrier layer, a hole barrier layer, an electron injection layer, an electron transport layer, and an exciton barrier layer. In one embodiment, the hole transport layer may be a hole injection and transport layer having a hole injection function, and the electron transport layer may be an electron injection and transport layer having an electron injection function. An example of an organic electroluminescence device is shown in FIG. 1 .

Emissive layer:

In one embodiment, the light emitting layer is a layer in which holes and electrons respectively injected from the anode and the cathode recombine to form excitons. In one embodiment, the layer emits light.

In one embodiment, only the light emitting material is used as the light emitting layer. In one embodiment, the light emitting layer includes a light emitting material and a host material. In one embodiment, the light emitting material is one or more compounds of the general formula (1). In one embodiment, singlet excitons and triplet excitons generated in the light emitting material are confined within the light emitting material in order to improve the light emission efficiency of the organic electroluminescence element and the organic light luminescence element. In one embodiment, a host material is used in addition to the light emitting material in the light emitting layer. In one embodiment, the host material is an organic compound. In one embodiment, the organic compound has singlet excitation energy and triplet excitation energy, at least one of which is higher than those of the light emitting material of the present invention. In one embodiment, singlet excitons and triplet excitons generated in the light emitting material of the present invention are confined in molecules of the light emitting material of the present invention. In one embodiment, singlet and triplet excitons are sufficiently constrained to improve the light radiation efficiency. In one embodiment, even though high light radiating efficiency is still obtained, singlet excitons and triplet excitons are not sufficiently constrained, that is, the host material capable of achieving high light emitting efficiency is not particularly limited. can be used in the invention. In one embodiment, light emission occurs in the light emitting material in the light emitting layer of the device of the present invention. In one embodiment, the emitted light includes both fluorescence and delayed fluorescence. In one embodiment, the emitted light includes radiation from a host material. In one embodiment, the emitted light is composed of radiation from a host material. In one embodiment, the emitted light includes emitted light from a compound represented by General Formula (1) and emitted light from a host material. In one embodiment, TADF molecules and host materials are used. In one embodiment, TADF is an assist dopant.

When using the compound represented by general formula (1) as an assist dopant, it is possible to employ various compounds as a light emitting material (preferably a fluorescent material). Examples of such light-emitting materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, and anthryl derivatives. , pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, It is possible to use thiazole derivatives, derivatives having metals (Al, Zn), and the like. These exemplary skeletons may or may not have substituents. Moreover, you may combine these exemplified skeletons.

Below, the light emitting material which can be used in combination with the assist dopant represented by General formula (1) is illustrated.

[Formula 22-1]

[Formula 22-2]

[Formula 22-3]

[Formula 22-4]

Moreover, the compound described in Paragraph 0220 - 0239 of WO2015/022974 can also be employ|adopted especially preferably as a light emitting material used with the assist dopant represented by General formula (1).

In one embodiment, when using a host material, the amount of the compound of the present invention as a light emitting material contained in the light emitting layer is 0.1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention as a light emitting material contained in the light emitting layer is 1% by weight or more. In one embodiment, when using a host material, the amount of the compound of the present invention as a light emitting material contained in the light emitting layer is 50% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention as a light emitting material contained in the light emitting layer is 20% by weight or less. In one embodiment, when using a host material, the amount of the compound of the present invention as a light emitting material contained in the light emitting layer is 10% by weight or less.

In one embodiment, the host material of the light emitting layer is an organic compound having a hole transport function and an electron transport function. In one embodiment, the host material of the light emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In one embodiment, the host material of the light emitting layer is an organic compound having a high glass transition temperature.

In some embodiments, the host material is selected from the group consisting of:

[Formula 23-1]

[Formula 23-2]

In one embodiment, the light emitting layer includes two or more kinds of TADF molecules having different structures. For example, a light emitting layer containing three types of materials having higher excitation singlet energy levels in the order of the host material, the first TADF molecule, and the second TADF molecule can be used. At this time, in both the first TADF molecule and the second TADF molecule, the difference ΔE _ST between the lowest singlet excitation energy level and the lowest triplet excitation energy level of 77K is preferably 0.3 eV or less, more preferably 0.25 eV or less, and 0.2 eV or less. It is more preferably eV or less, more preferably 0.15 eV or less, still more preferably 0.1 eV or less, even more preferably 0.07 eV or less, still more preferably 0.05 eV or less, still more preferably 0.03 eV or less, and 0.01 eV or less It is particularly preferred that it is eV or less. The content of the first TADF molecules in the light emitting layer is preferably greater than the content of the second TADF molecules. In addition, the content of the host material in the light emitting layer is preferably greater than the content of the second TADF molecule. The content of the first TADF molecules in the light emitting layer may be greater than or less than the content of the host material, or may be the same. In one embodiment, the composition in the light emitting layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecule, and 0.1 to 30% by weight of the second TADF molecule. In one embodiment, the composition in the light emitting layer may be 20 to 45% by weight of the host material, 50 to 75% by weight of the first TADF molecule, and 5 to 20% by weight of the second TADF molecule. In one embodiment, the light emission quantum yield φPL1 (A) by light excitation of the co-deposited film of the first TADF molecules and the host material (the content of the first TADF molecules in the co-deposited film = A% by weight), and the second TADF The light emission quantum yield φPL2(A) due to light excitation of the co-deposited film of the molecules and the host material (the content of the second TADF molecules in the co-deposited film = A% by weight) is the relational expression of φPL1(A) > φPL2(A) meets In one embodiment, the light emission quantum yield φPL2 (B) of the co-deposited film of the second TADF molecules and the host material (the content of the second TADF molecules in the co-deposited film = B% by weight), and the second TADF The light emission quantum yield φPL2(100) due to photoexcitation of a single film of molecules satisfies the relational expression of φPL2(B)>φPL2(100). In one embodiment, the light emitting layer may include three types of TADF molecules having different structures. The compound of the present invention may be any of a plurality of TADF compounds included in the light emitting layer.

In one embodiment, the light emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light emitting material. In one embodiment, the light emitting layer does not contain a metal element. In one embodiment, the light emitting layer can be composed of a material composed of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light emitting layer may be made of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light emitting layer may be made of a material composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms.

When the light emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescent material. As a preferred delayed fluorescent material, paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, and paragraphs 0059 to 0066 of WO2013/08108 0008 to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of Japanese Unexamined Patent Publication No. 2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of Japanese Unexamined Patent Publication No. 2013-116975, paragraphs 00327 to 00327 of WO2013/133359 and 0079 to 0084, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013/161437, paragraphs 0007 to 0041 and 0060 to 0069 of Japanese Laid-Open Patent Publication No. 2014-9352, paragraphs 0008 to 0048 and 0067 to of Japanese Laid-Open Patent Publication No. 2014-9224 0076, paragraphs 0013 to 0025 of JP 2017-119663, paragraphs 0013 to 0026 of JP 2017-119664, paragraphs 0012 to 0025 of JP 2017-222623, paragraph 2017-226838 0010 to 0050, paragraphs 0012 to 0043 of Japanese Laid-Open Patent Publication No. 2018-100411, and paragraphs 0016 to 0044 of WO2018/047853, which are compounds included in the general formula, particularly exemplary compounds, and include those capable of emitting delayed fluorescence. . Moreover, here, Unexamined-Japanese-Patent No. 2013-253121, WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895, WO2014/126200, WO2014/136758, WO2014/133121, WO2014 /136860, WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580, WO2014/203840, WO2015/002213, WO2015/016200, WO2015/019725, WO22201/07 / 108049, WO2015/080182, WO2015/072537, WO2015/080183, Japanese Patent Laid-Open No. 2015-129240, WO2015/129714, WO2015/129715, WO2015/133501, WO2015/1368815, WO2015/1368815 137244, WO2015/137202, WO2015/137136, WO2015/146541, and WO2015/159541, and those capable of emitting delayed fluorescence can be preferably employed. In addition, the said publication described in this paragraph is cited here as a part of this specification.

In the following, each member of the organic electroluminescent element and each layer other than the light emitting layer will be described.

write:

In some embodiments, the organic electroluminescence device of the present invention is supported by a substrate, and the substrate is not particularly limited, and is generally used in organic electroluminescence devices, such as glass, transparent plastic, Any one material formed by quartz and silicon may be used.

anode:

In some embodiments, the anode of the organic electroluminescence device is made of a metal, alloy, conductive compound, or combination thereof. In some embodiments, the metal, alloy or conductive compound has a high work function (4 eV or greater). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO ₂ and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film is used, such as IDIXO (In ₂ O ₃ -ZnO). In some embodiments, the anode is a thin film. In some embodiments, the thin film is fabricated by vapor deposition or sputtering. In some embodiments, the film is patterned by a photolithographic method. In some embodiments, when the pattern does not need to be highly precise (for example, about 100 μm or more), the pattern may be formed using a mask having a shape suitable for deposition or sputtering of an electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film forming method such as a printing method or a coating method is used. In some embodiments, when radiation passes through the anode, the anode has a transmittance of greater than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

cathode:

In some embodiments, the cathode is made of an electrode material such as a metal having a low work function (4 eV or less) (referred to as an electron injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ₂ O ₃ ) mixtures, indium, lithium-aluminum mixtures and rare earth elements. In some embodiments, a mixture of an electron injecting metal and a second metal, which is a stable metal with a higher work function than the electron injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al ₂ O ₃ ) mixtures, lithium-aluminum mixtures and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming a thin film of the electrode material by vapor deposition or sputtering. In some embodiments, the negative electrode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the cathode is between 10 nm and 5 μm. In some embodiments, the thickness of the cathode is 50-200 nm. In some embodiments, either the anode or cathode of the organic electroluminescence device is transparent or translucent in order to transmit radiation. In some embodiments, a transparent or translucent electroluminescent element enhances light radiant brightness.

In some embodiments, a transparent or translucent cathode is formed by forming the cathode from the conductive transparent material described above with respect to the anode. In some embodiments, the device includes an anode and a cathode, but both are transparent or translucent.

Injection layer:

The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the drive voltage, enhancing the optical radiance. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer may be disposed between the anode and the light emitting layer or hole transport layer, and between the cathode and the light emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, no injection layer is present.

Examples of preferable compounds that can be used as the hole injecting material are listed below.

[Formula 24]

Next, examples of preferable compounds that can be used as electron injecting materials are given.

[Formula 25]

barrier layer:

The barrier layer is a layer capable of preventing the diffusion of charges (electrons or holes) and/or excitons present in the light emitting layer to the outside of the light emitting layer. In some embodiments, the electron barrier layer is present between the light emitting layer and the hole transport layer, and prevents electrons from passing through the light emitting layer and reaching the hole transport layer. In some embodiments, the hole barrier layer is present between the light emitting layer and the electron transport layer, and prevents holes from passing through the light emitting layer and reaching the electron transport layer. In some embodiments, the barrier layer prevents excitons from diffusing out of the light emitting layer. In some embodiments, the electron barrier layer and the hole barrier layer constitute an exciton barrier layer. The term "electron barrier layer" or "exciton barrier layer" used herein includes a layer having both the functions of an electron barrier layer and an exciton barrier layer.

hole barrier layer:

The hole barrier layer functions as an electron transport layer. In some embodiments, during electron transport, the hole barrier layer prevents holes from reaching the electron transport layer. In some embodiments, the hole barrier layer increases the probability of recombination of electrons and holes in the light emitting layer. The material used for the hole barrier layer may be the same material as described above for the electron transport layer.

Examples of preferable compounds usable for the hole barrier layer are given below.

[Formula 26]

electron barrier layer:

The electron barrier layer transports holes. In some embodiments, during hole transport, the electron barrier layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron barrier layer increases the probability of recombination of electrons and holes in the light emitting layer. The material used for the electron barrier layer may be the same material as described above for the hole transport layer.

Specific examples of preferred compounds that can be used as electron barrier materials are given below.

[Formula 27]

Exciton barrier layer:

The exciton barrier layer prevents excitons generated through recombination of holes and electrons in the light emitting layer from diffusing to the electron transport layer. In some embodiments, the exciton barrier layer enables effective confinement of excitons in the light emitting layer. In some embodiments, the optical radiation efficiency of the device is improved. In some embodiments, the exciton barrier layer is adjacent to the light emitting layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton barrier layer is present on the anode side, the layer may be present between the hole transport layer and the light emitting layer and may be adjacent to the light emitting layer. In some embodiments, when the exciton barrier layer exists on the cathode side, the layer may be present between the light emitting layer and the cathode and may be adjacent to the light emitting layer. In some embodiments, a hole injection layer, an electron barrier layer, or the same layer exists between an anode and an exciton barrier layer adjacent to the light emitting layer on the anode side. In some embodiments, a hole injection layer, an electron barrier layer, a hole barrier layer, or the same layer exists between a cathode and an exciton barrier layer adjacent to the light emitting layer on the cathode side. In some embodiments, the exciton barrier layer contains singlet excitation energy and triplet excitation energy, and at least one of them is higher than the singlet excitation energy and triplet excitation energy of the light emitting material, respectively.

hole transport layer:

The hole transport layer contains a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has a plurality of layers.

In some embodiments, the hole transport material has one of hole injection or transport properties and electron barrier properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, and pyrazoline derivatives. , pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers and conductive polymer oligomers (particularly thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferable compounds that can be used as hole transport materials are given below.

[Formula 28]

electron transport layer:

The electron transport layer contains an electron transport material. In some embodiments, the electron transport layer is a monolayer. In some embodiments, the electron transport layer has multiple layers.

In some embodiments, the electron transport material only needs to have a function of transporting electrons injected from the cathode to the light emitting layer. In some embodiments, the electron transport material also functions as a hole barrier material. Examples of the electron transport layer that can be used in the present invention include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrane dioxide derivatives, carbodiimide, fluorenylidene methane derivatives, anthraquinodimethane , anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole derivative or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. Specific examples of preferable compounds that can be used as electron transport materials are given below.

[Formula 29]

In addition, examples of compounds suitable as materials that can be added to each organic layer are given. For example, adding as a stabilizing material or the like is conceivable.

[Formula 30]

Preferable materials usable for organic electroluminescence devices have been specifically exemplified, but materials usable in the present invention are not limitedly interpreted by the following exemplified compounds. In addition, even if it is a compound exemplified as a material having a specific function, it is also possible to divert it as a material having other functions.

device:

In some embodiments, the light emitting layer is included in the device. For example, devices include, but are not limited to, OLED valves, OLED lamps, displays for televisions, monitors for computers, mobile phones and tablets.

In some embodiments, an electronic device includes an OLED having at least one organic layer including an anode, a cathode, and a light emitting layer between the anode and the cathode.

In some embodiments, the constructs described herein may be included in a variety of photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the constructs may be useful for facilitating charge transfer or energy transfer within a device, and/or as a hole transport material. As the device, for example, an organic light emitting diode (OLED), an organic integrated circuit (OIC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic Solar cells (O-SC), organic optical detection devices, organic photoreceptors, organic field-quench devices (O-FQD), light emitting fuel cells (LEC) or organic laser diodes (O-Laser). can be heard

Valve or Ramp:

In some embodiments, an electronic device includes an OLED including at least one organic layer including an anode, a cathode, and a light emitting layer between the anode and the cathode.

In some embodiments, the device includes OLEDs with different colors. In some embodiments, a device includes an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (eg, RGB). In some embodiments, the combination of OLEDs is a combination of colors that are neither red nor green nor blue (eg orange and yellow green). In some embodiments, the combination of OLEDs is a combination of two, four or more colors.

In some embodiments, the device

a circuit board having a first surface having a mounting surface and a second surface opposite thereto, and defining at least one opening;

At least one OLED on the mounting surface, wherein the at least one OLED includes at least one organic layer including an anode, a cathode, and a light emitting layer between the anode and the cathode, and has a configuration for emitting light. of OLED,

a housing for a circuit board;

An OLED light having at least one connector disposed at an end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture.

In some embodiments, the OLED light has a plurality of OLEDs mounted on a circuit board so that light is emitted in a plurality of directions. In some embodiments, some of the light emitted in the first direction is polarized and emitted in the second direction. In some embodiments, a reflector is used to polarize the generated light in a first direction.

Display or Screen:

In some embodiments, the light emitting layer of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using a process such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photo plate structure useful for two-sided etching to provide pixels of unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. By designing the corresponding artwork pattern, it is possible to place very steep and narrow tie bars between pixels in the vertical direction and wide-ranging square openings in the horizontal direction. This enables the fine patterning of pixels required for high-resolution displays while optimizing the chemical vapor deposition onto the TFT back plane.

Internal patterning of pixels makes it possible to construct three-dimensional pixel openings of various aspect ratios in the horizontal and vertical directions. Also, the use of imaged "stripes" or halftone circles in pixel areas is protected from etching in particular areas until these particular patterns are removed from the substrate by undercutting them. At that time, all pixel areas are processed with the same etching rate, but their depths are varied by halftone patterns. By changing the size and spacing of the halftone patterns, different etchings with varying degrees of protection within the pixel are possible, enabling the localized deep etching required to form steep vertical squares.

A preferred material for the deposition mask is invar. Invar is a metal alloy cold-rolled into a long thin sheet in a steel mill. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable and low-cost method for forming an opening region in a deposition mask is a method by wet chemical etching.

In some embodiments, the screen or display pattern is a matrix of pixels on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (eg photolithography and e-beam lithography). In some embodiments, the screen or display pattern is processed using wet chemical etching. In a further embodiment, the screen or display pattern is processed using plasma etching.

Manufacturing method of the device:

An OLED display is generally manufactured by forming a large-sized mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and a source/drain electrode on a base substrate, and a flattening film is applied to the TFT to form a pixel electrode, a light emitting layer, a counter electrode and An encapsulation layer is sequentially formed over time, and is formed by cutting from the mother panel.

An OLED display is generally manufactured by forming a large-sized mother panel and then cutting the mother panel into cell panel units. Usually, each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and a source/drain electrode on a base substrate, and a flattening film is applied to the TFT to form a pixel electrode, a light emitting layer, a counter electrode and An encapsulation layer is sequentially formed over time, and is formed by cutting from the mother panel.

In another aspect of the present invention, a method for manufacturing an organic light emitting diode (OLED) display is provided, the method comprising:

A step of forming a barrier layer on the base substrate of the mother panel;

forming a plurality of display units on the barrier layer in units of cell panels;

forming an encapsulation layer on each of the display units of the cell panel;

and applying an organic film to the interface between the cell panels.

In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and ends of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in smoothly cutting the mother panel into cell panel units.

In some embodiments, a thin film transistor (TFT) layer has a light emitting layer, a gate electrode, and a source/drain electrode. Each of the plurality of display units may have a thin film transistor (TFT) layer, a flattening film formed on the TFT layer, and a light emitting unit formed on the flattening film, and the organic film applied to the interface portion is the flattening film. It is formed of the same material as the material of, and is formed simultaneously with the formation of the planarization film. In some embodiments, the light emitting unit is connected to the TFT layer by a passivation layer, a flattening film therebetween, and an encapsulation layer that covers and protects the light emitting unit. In some embodiments of the manufacturing method, the organic film is connected neither to the display unit nor to the encapsulation layer.

Each of the organic film and the flattening film may contain any one of polyimide and acryl. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method also includes, before forming a barrier layer on one surface of a base substrate formed of polyimide, a step of mounting a carrier substrate formed of a glass material on another surface of the base substrate, and before cutting along the interface, A step of separating the carrier substrate from the base substrate may be included. In some embodiments, the OLED display is a flexible display.

In some embodiments, the passivation layer is an organic film disposed over the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the flattening film is formed of polyimide or acrylic, similar to the organic film formed at the end of the barrier layer. In some embodiments, in the manufacture of an OLED display, the planarization film and organic film are formed simultaneously. In some embodiments, the organic film may be formed at an end portion of the barrier layer, whereby a part of the organic film directly contacts the base substrate, and the remaining portion of the organic film surrounds the end portion of the barrier layer. , in contact with the barrier layer.

In some embodiments, the light emitting layer has a pixel electrode, a counter electrode, and an organic light emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source/drain electrode of the TFT layer.

In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, whereby the organic light emitting layer emits light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light emitting unit is referred to as a display unit.

In some embodiments, the encapsulation layer that covers the display unit and prevents permeation of external moisture may be formed on a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface unit is disposed at intervals from each of the plurality of display units. In some embodiments, the organic film is formed in such a way that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the ends of the barrier layer.

In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide. In some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and then the carrier substrate is separated.

In some embodiments, the barrier layer is formed on the surface of the base substrate on the opposite side of the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of the mother panel, while a barrier layer is formed according to the size of each cell panel, whereby a groove is formed in an interface portion between the barrier layers of the cell panel. Each cell panel can be cut along the groove.

In some embodiments, the above manufacturing method further includes a step of cutting along the interface, wherein grooves are formed in the barrier layer, and at least a part of the organic film is formed in the grooves, so that the grooves are formed in the base substrate. do not penetrate into In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a flattening film, which is an organic film, are disposed on the TFT layer to cover the TFT layer. At the same time as a flattening film made of, for example, polyimide or acrylic is formed, the grooves of the interface portion are covered with an organic film, for example, made of polyimide or acrylic. This prevents cracking by absorbing the impact generated when each cell panel is cut along the groove in the interface portion to the organic film. That is, when all the barrier layers are completely exposed without the organic film, when each cell panel is cut along the groove at the interface portion, the generated shock is transferred to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the grooves of the interface between the barrier layers are covered with an organic film, and each cell panel is softly cut to break the barrier layer in order to absorb the impact that can be transmitted to the barrier layer without the organic film. You may prevent this from occurring. In one embodiment, the organic film and the flattening film covering the grooves of the interface portion are spaced apart from each other. For example, when the organic film and the flattening film are connected to each other as one layer, moisture from the outside may enter the display unit through a portion where the flattening film and the organic film remain, so that the organic film and the flattening film may enter the display unit. The films are spaced apart from each other, just as organic films are spaced apart from the display unit.

In some embodiments, the display unit is formed by forming a light emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is emitted to a carrier substrate, the carrier substrate is separated from the base substrate due to a difference in coefficient of thermal expansion between the carrier substrate and the base substrate.

In some embodiments, the mother panel is cut in units of cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, since the groove of the interface portion along which the mother panel is cut is covered with an organic film, the organic film absorbs impact during cutting. In some embodiments, cracking in the barrier layer can be prevented during cutting.

In some embodiments, the method reduces the reject rate of a product, thereby stabilizing its quality.

Another aspect is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to an end of the barrier layer.

Example

The characteristics of the present invention will be described in more detail by way of synthetic examples and examples below. Materials, processing details, processing procedures, and the like described below can be appropriately changed without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be limitedly interpreted by the specific examples shown below. In addition, the evaluation of luminous properties was carried out using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics) It was performed using a spectroradiometer (manufactured by Topcon: SR-3) and a streak camera (model C4334 manufactured by Hamamatsu Photonics Co., Ltd.).

(Synthesis Example 1) Synthesis of Compound C1

[Formula 31]

Under a nitrogen stream, potassium carbonate (1.04 g, 7.5 mmol), benzofuro[2,3-c]carbazole (1.61 g, 6.3 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.60 mmol, 2.5 mmol) was reacted in dimethylformamide (20 mL) at 100°C for 9 hours. Then, it returned to room temperature, water and methanol were added, and reaction was stopped. The precipitated yellow solid was filtered, and water was purified by silica gel column chromatography (toluene) and reprecipitation (toluene/methanol) to obtain compound C1 (1.33 g, yield 76%) as a yellow solid.

1H NMR _{(400MHz, CDCl 3} ^, δ): 8.49 (s, 1H), 8.43 (d, J=7.6Hz, 2H), 7.96-7.91 (m, 4H), 7.70 (d, J=7.6Hz, 2H) ), 7.47-7.36 (m, 8H), 7.14-7.11 (m, 2H), 7.10-7.07 (m, 2H), 6.52-6.46 (m, 3H), 6.37 (t, J=7.6 Hz, 2H).

MS (ASAP): 715.34 (M+H ⁺ ). Calcd for C ₅₀ H ₂₆ N ₄ O ₂ : 714.21.

(Synthesis Example 2) Synthesis of Compound C2

[Formula 32]

Compound C1 (2.40 g, 3.4 mmol), 4-bromobenzonitrile (1.17 g, 5.0 mmol), potassium carbonate (0.93 g, 6.7 mmol), 2-ethylhexanoic acid (0.10 mg, 0.7 mmol), tricyclo Hexylphosphine (0.10 g, 0.5 mmol) and dichlorobis(triphenylphosphine)palladium (0.20 g, 0.3 mmol) were dissolved in xylene (30 mL) under a nitrogen stream, and the mixture was stirred at 120°C for 18 hours. The mixture was returned to room temperature, and insoluble matter was removed by celite filtration. After concentrating the filtrate by distillation under reduced pressure, the residue was purified by silica gel column chromatography (chloroform/hexane = 2/1) and reprecipitation (toluene/methanol) to obtain compound C2 as a white solid (1.90 g, Yield 68%) was obtained.

¹ H NMR (400 MHz, CDCl ₃ , δ): 8.43 (d, J=7.6 Hz, 2H), 8.00-7.92 (m, 8H), 7.70 (d, J=8.0 Hz, 2H), 7.48-7.36 (m , 8H), 7.19 (d, J = 8.0 Hz, 2H), 7.14 (d, J = 8.0 Hz, 2H), 6.54-6.50 (m, 3H), 6.40 (t, J = 7.6 Hz, 2H).

MS (ASAP): 816.45 (M+H ⁺ ). Calcd for C ₅₇ H ₂₉ N ₅ O ₂ : 815.23.

(Synthesis Example 3) Synthesis of Compound C3

[Formula 33]

Under a nitrogen stream, potassium carbonate (1.22 g, 8.8 mmol), benzofuro[2,3-c]carbazole (2.00 g, 7.4 mmol) and 4,6-difluoro-5-phenylisophthalonitrile (0.77 mmol, 3.0 mmol) was reacted in dimethylformamide (36 mL) at 80°C for 2 hours. Then, it returned to room temperature, water was added, and reaction was stopped. Chloroform was added to the reaction mixture to separate the mixture, and the organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain compound C3 (2.25 g, yield 90%) as a yellow solid.

1H NMR _{(400MHz, CDCl 3} ^, δ): 8.44 (s, 1H), 8.22 (d, J=5.2Hz, 2H), 7.92 (t, J=7.2Hz, 2H), 7.88-7.81 (m, 2H) ), 7.69(d, J=8.0Hz, 2H), 7.45-7.40(m, 2H), 7.38-7.33(m, 2H), 7.27-7.26(m, 1H), 7.22(t, J=8.4Hz, 1H), 7.07-6.95 (m, 4H), 6.49-6.46 (m, 3H), 6.40-6.36 (m, 2H), 2.56 (d, J=7.2 Hz, 6H).

MS(ASAP): 743.28 [(M+H) ⁺ , cal. C ₅₂ H ₃₁ N ₄ O ₂ , 743.24].

(Synthesis Example 4) Synthesis of Compound C4

[Formula 34]

Sodium hydride (0.30 g, 7.5 mmol) and 11-phenyl-11,12-dihydroindolo[2,3-a]carbazole (2.08 g, 6.3 mmol) were dissolved in THF (20 mL) at room temperature under a nitrogen stream. After stirring for 1 hour, 4,6-difluoro-5-phenylisophthalonitrile (1.50 g, 6.24 mmol) dissolved in tetrahydrofuran (50 ml) was added dropwise. After reacting at room temperature for 5 hours, water was added to stop the reaction. Chloroform was added to the reaction mixture to separate the mixture, and the organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain intermediate 1 (1.82 g, yield 53%) as a yellow solid.

1H NMR (400MHz, CDCl ³ , δ): 8.10 ( _d , J=8.4Hz, 1H), 7.99 (d, J=7.6Hz, 1H), 7.78 (s, 1H), 7.61 (d, J=6.4 Hz, 1H), 7.48-7.40 (m, 4H), 7.36-7.20 (m, 7H), 6.84-6.82 (br, 1H), 6.70 (t, J=7.6Hz, 1H), 6.40 (t, J= 7.6Hz, 2H), 6.06(br, 1H); MS(ASAP): 553.70 [(M+H) ⁺ , cal. C ₃₈ H ₂₂ FN ₄ , 553.18].

Under a nitrogen stream, potassium carbonate (0.36g, 2.6mmol), benzofuro[2,3-c]carbazole (0.54g, 2.1mmol) and intermediate 1 (0.96mmol, 1.7mmol) were mixed with dimethylformamide (17mL). ), and reacted at room temperature for 4 hours. The reaction was stopped by adding water, chloroform was added to the reaction mixture, the mixture was separated, and the organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain Compound C4 (1.36 g, yield 99%) as a yellow solid.

¹ H NMR (400 MHz, CDCl ₃ , δ): 8.78 (s, 1.00), 8.55 (d, J=8.8 Hz, 0.54), 8.27-8.19 (m, 2.38), 8.02-7.97 (m, 1.55), 7.89 -7.83 (m, 2.85), 7.94-7.75 (m, 1.99), 7.70-7.62 (m, 1.98), 7.59-7.43 (m, 6.17), 7.39-7.34 (m, 0.51), 7.29-7.26 (m, 2.61), 7.21-7.16(m, 1.02), 7.06-6.99(m, 1.00), 6.81(br, 0.90), 6.67-6.61(m, 1.00), 6.15(t, J=7.6Hz, 0.5), 6.09 (t, J = 7.6 Hz, 0.5), 5.91 (br, 1.87), 5.57 (br, 0.90), 5.29 (br, 0.90); MS(ASAP): 790.31 [(M+H) ⁺ , cal. C ₅₆ H ₃₂ N ₄ O, 790.25].

(Synthesis Example 5) Synthesis of Compound C5

[Formula 35]

Under a nitrogen stream, sodium hydride (0.30 g, 7.5 mmol) and 5-phenyl-5,12-dihydroindolo[3,2-a]carbazole were stirred in THF (50 mL) at room temperature for 1 hour, followed by stirring in THF 4,6-difluoro-5-phenylisophthalonitrile (1.49 g, 6.20 mmol) dissolved in (50 ml) was added dropwise. After reacting at room temperature for 15 hours, the reaction was stopped with water. Chloroform was added to the reaction mixture to separate the mixture, and the organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain intermediate 2 (1.70 g, yield 50%) as a yellow solid.

1H NMR (400MHz, CDCl ³ , δ): 9.05 ( _d , J=6.4Hz, 1H), 8.16 (d, J=8.8Hz, 1H), 8.09-8.07 (m, 1H), 7.72-7.68 (m , 2H), 7.61-7.57 (m, 3H), 7.37-7.29 (m, 2H), 7.27-7.19 (m, 4H), 7.14-7.02 (m, 2H), 6.99-6.95 (m, 4H), 6.21 (d, J=8.0Hz, 1H).

MS(ASAP): 553.40 [(M+H) ⁺ , cal. C ₃₈ H ₂₂ FN ₄ , 553.18].

Under a nitrogen stream, potassium carbonate (0.43g, 3.1mmol), benzofuro[2,3-c]carbazole (0.66g, 2.6mmol) and intermediate 2 (1.30mmol, 2.4mmol) were mixed with dimethylformamide (25mL). ), and reacted at room temperature for 4 hours. The reaction was stopped by adding water, chloroform was added to the reaction mixture, the mixture was separated, and the organic layer was dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain compound C5 (1.63 g, yield 88%) as a yellow solid.

1H NMR _{(400MHz, CDCl 3} ^, δ): 9.44 (s, 1H), 8.22-8.17 (m, 1H), 8.12-8.07 (m, 1H), 7.76 (d, J=8.0Hz, 1H), 7.69 -7.26 (m, 17H), 7.08 (d, J=8.4 Hz, 1H), 6.54-6.49 (m, 1H), 6.40-6.03 (m, 5H).

MS(ASAP): 790.37 [(M+H) ⁺ , cal. C ₅₆ H ₃₂ N ₄ O, 790.25].

(Synthesis Example 6) Synthesis of Compound C6

[Formula 36]

Under a nitrogen stream, potassium phosphate (1.74 g, 8.2 mmol), 5-phenyl-5,12-dihydroindolo[3,2-a]carbazole (2.28 g, 6.8 mmol) and 4,6-difluoro -5-phenylisophthalonitrile (0.66 g, 2.7 mmol) was reacted in dimethylformamide (30 mL) at 110°C for 6 hours. After the reaction, the reaction was stopped by adding water at room temperature, chloroform was added to the reaction mixture, the mixture was separated, and the organic layer was dried with magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) to obtain compound C6 (0.97 g, yield 41%) as a yellow solid.

1H NMR _{(400MHz, CDCl 3} ^, δ): 9.57 (s, 1H), 8.01 (d, J=7.6Hz, 2H), 7.91 (d, J=8.4Hz, 2H), 7.64-7.60 (m, 4H) ), 7.54-7.50(m, 4H), 7.42-7.35(m, 10H), 7.26(t, J=8.0Hz, 2H), 7.22-7.19(m, 2H), 6.91(d, J=8.4Hz, 2H), 6.52-6.49 (m, 2H), 6.21 (t, J=7.2 Hz, 1H), 5.78 (t, J=8.0 Hz, 2H), 5.22 (d, J=7.6 Hz, 2H).

MS(ASAP): 865.47 [(M+H) ⁺ , cal. C ₆₂ H ₃₇ N ₆ , 865.30].

(Synthesis Example 7) Synthesis of Compound C7

[Formula 37]

Under a nitrogen stream, sodium hydride (0.19g, 4.7mmol) and benzofuro[3,2-c]carbazole (1.02g, 4.0mmol) were stirred in tetrahydrofuran (15mL) at 0°C for 30 minutes, 4,6-difluoro-5-phenylisophthalonitrile was added. After raising the temperature of the reaction solution to 40°C and reacting for 6 hours, the temperature was returned to room temperature and the reaction was stopped with water and methanol. The precipitated yellow solid was filtered, and the water was purified by silica gel column chromatography (toluene/hexane = 4/1) and reprecipitation (toluene/methanol) to obtain compound C7 as a yellow solid (0.98 g, yield 78%) got

¹ H NMR (400 MHz, CDCl ₃ , δ): 8.44 (d, J=8.0 Hz, 2H), 7.99-7.95 (m, 4H), 7.89-7.86 (m, 2H), 7.73-7.63 (m, 5H) , 7.49-7.45(m, 4H), 7.42-7.37(m, 4H), 7.25(d, J=8.4Hz, 2H), 7.23(d,J=8.8Hz, 2H), 6.56-6.50(m, 3H) ), 6.40 (t, J=7.6 Hz, 2H).

MS (ASAP): 791.26 (M+H ⁺ ). Calcd for C ₅₆ H ₃₀ N ₄ O ₂ : 790.24

(Synthesis Example 8) Synthesis of Compound C8

[Formula 38]

Under a nitrogen stream, sodium hydride (0.49g, 11.8mmol) and benzofuro[3,2-c]carbazole (2.54g, 9.9mmol) were stirred in tetrahydrofuran (20mL) at 0°C for 30 minutes, 4,5-difluoro-6-phenylisophthalonitrile was added. After returning the reaction solution to room temperature and reacting at room temperature for 6 hours, the reaction was stopped with water and methanol. The precipitated yellow solid was filtered, and the water was purified by silica gel column chromatography (toluene/chloroform = 10/1) and reprecipitation (toluene/methanol) to obtain compound C8 as a yellow solid (0.48 g, yield 17%) got

¹ H NMR (400 MHz, CDCl ₃ , δ): (With the presence of stereoisomers in the sample, the proton number is displayed as a relative ratio.) 8.53(s, 1H), 8.12(t, J=7.6Hz, 1H ), 7.97-7.94(m, 1H), 7.89-7.74(m, 2H), 7.67(d, J=8.4Hz, 0.5H), 7.59-7.50(m, 3H), 7.45(d, J=8.4Hz) , 0.5H), 7.41-7.28 (m, 4H), 7.22-7.17 (m, 0.5H), 7.14-6.97 (m, 10H), 6.90-6.84 (m, 2.5H).

MS (ASAP): 715.38 (M+H ⁺ ). Calcd for C ₅₀ H ₂₆ N ₄ O ₂ : 714.21

(Synthesis Example 9) Synthesis of Compound C9

[Formula 39]

Under a nitrogen stream, cesium carbonate (1.30 g, 4.0 mmol), 5-phenyl-5,11-dihydroindolo[3,2-a]carbazole (0.78 g, 2.3 mmol) and 4,6-difluoro -5-phenylisophthalonitrile (0.24 g, 1.0 mmol) was reacted in dimethylformamide (20 mL) at 80°C for 12 hours. After the reaction, the reaction was stopped by adding water at room temperature, chloroform was added to the reaction mixture, the mixture was separated, and the organic layer was dried with magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (toluene) and reprecipitation (toluene/methanol) to obtain compound C9 (0.17 g, yield 22%) as a yellow solid.

1H NMR (400MHz, CDCl ³ , δ): 8.53 ( _d , J=7.6Hz, 1H), 8.21 (d, J=8.0Hz, 1H), 8.15 (d, J=8.0Hz, 1H), 7.89- 7.96(m,4H), 7.85(s, 1H), 7.78(s, 1H), 7.07-7.66(m, 22H), 6.95(d, J=8.0Hz, 1H), 6.40-6.58(m, 3H) , 6.34(t, J=8.0 Hz, 2H).

MS (ASAP): 865.58 (M+H ⁺ ). Calcd for C ₆₂ H ₃₆ N ₆ : 864.30

(Synthesis Example 10) Synthesis of Compound C10

Compound C10 was synthesized by the same method as in Synthesis Example 1 (yield: 84%).

[Formula 40]

¹ H NMR (400 MHz, CDCl ₃ , δ): 8.62 (s, 2H), 8.51 (s, 1H), 7.99-7.90 (m, 4H), 7.79-7.71 (m, 6H), 7.69-7.64 (m, 2H), 7.52-7.44(m, 6H), 7.39-7.35(m, 4H), 7.21-7.18(m, 2H), 7.09-7.06(m, 2H), 6.58-6.50(m, 3H), 6.41( t, J = 8.4 Hz, 2H).

MS (ASAP): 867.50 (M+H ⁺ ). Calcd for C ₆₂ H ₃₄ N ₄ O ₂ : 866.27.

(Synthesis Example 11) Synthesis of Compound C11

Compound C11 was synthesized by the same method as in Synthesis Example 1 (yield: 78%).

[Formula 41]

1H NMR _{(400MHz, CDCl 3} ^, δ): 8.62 (s, 2H), 8.51 (s, 1H), 7.96-7.91 (m, 4H), 7.72 (d, J=8.2Hz, 2H), 7.70-7.64 (m, 2H), 7.46-7.37 (m, 2H), 7.21-7.19 (m, 2H), 7.09-7.06 (m, 2H),

MS(ASAP): 882.21(M+H ⁺ ). Calcd for C ₆₂ H ₁₉ D ₁₅ N ₄ O ₂ : 881.36.

(Synthesis Example 12) Synthesis of Compound C12

Compound C12 was synthesized by the same method as in Synthesis Example 1 (yield: 78%).

[Formula 42]

¹ H NMR (400 MHz, DMSO, δ): 9.48 (s, 1 H), 8.51 (s, 1 H), 8.29 (d, J = 8.4 Hz, 4 H), 8.19 (d, J = 8.4 Hz, 4 H), 7.91 (m J=8.4Hz, 4H), 7.84(t, J=6.8Hz, 4H), 7.45(t, J=6.8Hz, 4H), 6.73(t, J=7.2Hz ,2H), 6.38(t, J=7.2Hz ,3H),

MS (ASAP): 895.35 (M+H ⁺ ). Calcd for C ₆₂ H ₃ 0 N ₄ O ₄ : 894.23

(Synthesis Example 13) Synthesis of Compound C13

Compound C13 was synthesized by the same method as in Synthesis Example 1 (yield: 64%).

[Formula 43]

¹ H NMR (400 MHz, CDCl ₃ , δ): 8.82-8.76 (m, 4H), 8.45 (s, 1H), 7.64-7.32 (m, 22H), 7.21 (d, J=9.2Hz, 2H), 7.08 -7.05(m, 2H), 6.47-6.44(m, 3H), 6.32(t, J=9.2Hz,2H).

MS (ASAP): 865.27 (M+H ⁺ ). Calcd for C ₆₂ H ₃₆ N ₆ : 864.30

(Synthesis Example 14) Synthesis of Compound C14

Compound C14 was synthesized by the same method as in Synthesis Example 1 (yield: 47%).

[Formula 44]

1H NMR _{(400MHz, CDCl 3} ^, δ): 8.47 (s, 1H), 8.19-8.10 (m, 4H), 7.68-7.51 (m, 10H), 7.38-7.26 (m, 6H), 7.20-7.14 ( m, 2H), 7.06-6.98 (m, 4H), 6.74 (t, J=7.6 Hz, 2H), 6.47-6.44 (m, 3H), 6.31 (t, J=7.6 Hz, 2H).

MS (ASAP): 865.37 (M+H ⁺ ). Calcd for C ₆₂ H ₃₆ N ₆ : 864.30

(Examples 1 to 9, Comparative Examples 1 to 4) Fabrication and evaluation of thin films

Compound C1 and Host1 were deposited from different deposition sources on a quartz substrate by a vacuum deposition method under a vacuum degree of less than 1×10 ^-3 Pa, and a thin film having a concentration of Compound C1 of 20% by weight was formed to a thickness of 100 nm, It is set as the doped thin film of Example 1.

Instead of compound C1, compounds C2 to C9 were used, respectively, to obtain thin films of Examples 2 to 9 sequentially. In addition, a thin film of Comparative Example 1 was similarly obtained using Compound A and PPF. In addition, each compound used as a light emitting material in Examples and Comparative Examples in the present specification was used after sublimation purification before use.

As a result of irradiating each obtained thin film with excitation light of 300 nm, photoluminescence was confirmed for all the thin films. The lifetime of delayed fluorescence (τ _d ) was obtained from the transient decay curve of luminescence, and the relative value for Comparative Example 1 was calculated based on the lifetime of Comparative Example 1. The results were as shown in the table below. It was confirmed that the delayed fluorescence lifetime (τ _d ) of Examples 1 to 9 was short.

[Table 2]

(Examples 10 to 14, Comparative Example 2) Preparation of organic electroluminescence device

Each thin film was laminated at a vacuum degree of 1×10 ^-6 Pa by vacuum evaporation on a glass substrate having an anode made of indium tin oxide (ITO) with a film thickness of 100 nm. First, HATCN was formed on ITO to a thickness of 10 nm, and NPD was formed thereon to a thickness of 30 nm. Subsequently, TrisPCz was formed thereon to a thickness of 10 nm, and Host1 was further formed thereon to a thickness of 5 nm. Next, compound C1 and Host1 were co-evaporated from different evaporation sources, respectively, to form a light emitting layer having a thickness of 30 nm. At this time, the concentration of compound C1 was 35% by weight. SF3TRZ was formed thereon to a thickness of 10 nm, and further, SF3TRZ and Liq were co-evaporated thereon from different deposition sources to form a thickness of 30 nm. At this time, SF3TRZ:Liq (weight ratio) was 7:3. Further, a cathode was formed by forming Liq to a thickness of 2 nm and then depositing aluminum (Al) to a thickness of 100 nm. According to the above procedure, the organic electroluminescent device of Example 10 was fabricated.

Instead of compound C1, compound C2, compound C3, compound C4, compound C6, and comparative compound A were respectively used to prepare organic electroluminescence devices of Examples 11 to 14 and Comparative Example 2 in order.

(evaluation)

As a result of measuring the x and y of the CIE chromaticity coordinates for light emission of the organic electroluminescence device of Example 10, it was confirmed that the chromaticity was good, with x = 0.26 and y = 0.57. In addition, the time (LT95) until the emission intensity at 12.6 mA/cm ² of each organic electroluminescence device of Example 10 and Comparative Example 2 decreased to 95% was measured, and the LT95 of Comparative Example 2 was measured. The relative value when is set to 1 was calculated. The results were as shown in the table below. The organic electroluminescent device of Example 10 had significantly improved device life (device durability).

[Table 3]

[Formula 45]

1 description
2 anode
3 hole injection layer
4 hole transport layer
5 light emitting layer
6 electron transport layer
7 cathode

Claims (21)

A compound represented by the following general formula (1).
[Formula 1]

[In Formula (1),
R is a hydrogen atom, a heavy hydrogen atom, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group bonded to a carbon atom;
Ar is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group bonded with a carbon atom;
D ¹ and D ² each independently represent a donor group, and at least one of them is a heterocyclic condensed carbazol-9-yl group (the heterocyclic ring and the carbazole may be substituted).] The method of claim 1,
A compound in which the compound is represented by the following general formula (2).
[Formula 2]

The method of claim 1,
A compound in which the compound is represented by the following general formula (3).
[Formula 3]

The method according to any one of claims 1 to 3,
A compound wherein D ¹ and D ² are the same. The method according to any one of claims 1 to 3,
A compound wherein D ¹ and D ² are different. The method according to any one of claims 1 to 5,
The heterocyclic ring condensed with the carbazol-9-yl group of the heterocyclic condensed carbazol-9-yl group is a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, or a substituted or unsubstituted pyrrole ring, , A compound in which other rings may be further condensed to the furan ring, the thiophene ring, and the pyrrole ring. The method according to any one of claims 1 to 6,
A compound wherein the heterocyclic condensed carbazol-9-yl group has a structure of any one of the following.
[Formula 4]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed.] The method according to any one of claims 1 to 6,
A compound wherein the heterocyclic condensed carbazol-9-yl group has a structure of any one of the following.
[Formula 5]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed.] The method according to any one of claims 1 to 6,
A compound wherein the heterocyclic condensed carbazol-9-yl group has a structure of any one of the following.
[Formula 6]

[In each of the above structures, the hydrogen atom may be substituted, but the heterocyclic ring is not further condensed. R' represents a hydrogen atom, a deuterium atom or a substituent.] The method according to any one of claims 1 to 9,
To the carbazol-9-yl group of the heterocyclic condensed carbazol-9-yl group, a substituted or unsubstituted furan ring, a substituted or unsubstituted thiophene ring, and a substituted or unsubstituted pyrrole ring (the furan ring, the above A compound in which two heterocycles selected from the group consisting of a thiophene ring and the pyrrole ring may be further condensed with other rings are condensed. The method according to any one of claims 1 to 10,
A compound in which the heterocyclic condensed carbazol-9-yl group has a structure in which a heterocyclic ring is condensed at the 1st and 2nd positions of the carbazole ring. The method according to any one of claims 1 to 10,
A compound in which the heterocyclic condensed carbazol-9-yl group has a structure in which heterocyclic rings are condensed at positions 2 and 3 of the carbazole ring. The method according to any one of claims 1 to 10,
A compound in which the heterocyclic condensed carbazol-9-yl group has a structure in which a heterocyclic ring is condensed at positions 3 and 4 of the carbazole ring. The method according to any one of claims 1 to 13,
A compound in which R and Ar are different. The method according to any one of claims 1 to 13,
A compound in which R is a hydrogen atom or a deuterium atom. The method according to any one of claims 1 to 15,
A compound in which Ar is a substituted or unsubstituted phenyl group or a substituted or unsubstituted pyridyl group. The method according to any one of claims 1 to 16,
A compound comprising an atom selected from the group consisting of a carbon atom, a hydrogen atom, a deuterium atom, a nitrogen atom, an oxygen atom, and a sulfur atom. A light emitting material comprising the compound according to any one of claims 1 to 17. A light emitting element comprising the compound according to any one of claims 1 to 17. The method of claim 19
The light-emitting element, wherein the light-emitting element has a light-emitting layer, and the light-emitting layer contains the compound and a host material. The method of claim 20
The light-emitting element has a light-emitting layer, the light-emitting layer contains the compound and a light-emitting material, and emits light mainly from the light-emitting material.

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